Jason Calacanis — The Knowledge Project #81

Timing & Small Bets

Jason Calacanis highlights the importance of timing in angel investing. He advises new investors to wait until a product is in the market and to talk to actual customers to reduce risk significantly. He also stresses the need to make small bets initially to learn and gather information before committing larger sums.

Bet small, see a lot of flops, and then continue to bet on the flops that are the strongest for you and conversely, likely the weakest for your opponents.

--- Jason Calacanis

Angel investing requires a mindset shift to handle numerous losses, with the understanding that a single successful investment can offset many failures 1.

   

Evaluating Founders

Evaluating startups involves assessing the founder's focus and resilience. Jason uses specific questions to gauge a founder's commitment and ability to persevere through challenges. He believes that the quality of an investment decision should be judged by the process and not just the outcome.

These businesses take a level of focus and commitment that is otherworldly.

--- Jason Calacanis

He also acknowledges the role of timing and geography in his investment successes, noting that many factors beyond picking skills contribute to outcomes 2.